Method for detecting purity of 3-cyclopentyl-3-hydrazinopropionitrile or salt thereof or hydrate of salt

Abstract

The invention provides a method for detecting the purity or content of 3-cyclopentyl-3-hydrazinopropionitrile or salt or hydrate thereof, and belongs to the field of analytical chemistry. The detection method comprises the step of detecting by adopting a gas chromatographic method, wherein the gas chromatographic method adopts a CAM gas chromatographic column or a DB-17 gas chromatographic column as a separation chromatographic column for separation. The detection method has the advantages of good separation degree, good peak pattern, simplicity in operation, simplicity, rapidness and the like.

Description

TECHNICAL FIELD

[0001] The present application relates to the field of analytical chemistry, in particular to a method for detecting the purity of 3-cyclopentyl-3-hydrazinylpropionitrile or its salt or its hydrate. BACKGROUND

[0002] 3-cyclopentyl-3-hydrazinylpropionitrile is a starting material for the synthesis of some drugs, for example: in patent application CN202180068688.5, 3-cyclopentyl-3-hydrazinylpropionitrile is used as a starting material for the synthesis of ruxolitinib (alias: ruxolitinib) or its salt.

[0003] 3-cyclopentyl-3-hydrazinylpropionitrile has no ultraviolet absorption and contains a strong base (hydrazinyl) group. When detected by gas chromatography, it is found that 3-cyclopentyl-3-hydrazinylpropionitrile has poor peak shape and serious tailing on most gas chromatography columns, which leads to inaccurate determination of its purity. As a starting material for the synthesis of drugs, relevant guidelines such as ICH Q11 (ICH: International Conference on Harmonization of Technical Requirements for Registration of Pharmaceuticals for Human Use; ICH Q11 is the Guideline for Drug Development and Manufacturing issued by ICH) require the purity of the starting material to be studied. At present, no method for detecting the purity of 3-cyclopentyl-3-hydrazinylpropionitrile has been reported.

[0004] Therefore, there is still a need for a method for detecting the purity of 3-cyclopentyl-3-hydrazinylpropionitrile or its salt or its hydrate, which has good peak shape, good accuracy and high separation degree. SUMMARY

[0005] To solve the above technical problems, the present application provides a method for detecting the purity of 3-cyclopentyl-3-hydrazinylpropionitrile or its salt or its hydrate.

[0006] A method for detecting the purity of 3-cyclopentyl-3-hydrazinylpropionitrile or its salt or its hydrate, the detection method comprising: preparing a test solution and detecting by gas chromatography;

[0007] The preparation method of the test solution comprises: derivatizing 3-cyclopentyl-3-hydrazinylpropionitrile with acetone to obtain the test solution; or derivatizing the salt of 3-cyclopentyl-3-hydrazinylpropionitrile or the hydrate of the salt of 3-cyclopentyl-3-hydrazinylpropionitrile with acetone, then extracting with dichloromethane to obtain the test solution; or dissolving the salt of 3-cyclopentyl-3-hydrazinylpropionitrile or the aqueous solution of the salt of 3-cyclopentyl-3-hydrazinylpropionitrile with an aqueous alkali solution, then extracting with dichloromethane to obtain the test solution.

[0008] In some embodiments, the gas chromatography employs a CAM gas chromatography column as the separation chromatographic column for separation, and the detection method further comprises preparation of a test sample solution, wherein the preparation of the test sample solution comprises method S1, method S2, method S3 or method S4:

[0009] Method S1: after derivatization of 3-cyclopentyl-3-hydrazinylpropionitrile with acetone, a test sample solution is obtained; or

[0010] Method S2: after derivatization of a salt of 3-cyclopentyl-3-hydrazinylpropionitrile or a hydrate of a salt of 3-cyclopentyl-3-hydrazinylpropionitrile with acetone, extraction is performed with dichloromethane, and a test sample solution is obtained from the dichloromethane layer; or

[0011] Method S3: after dissolution of a salt of 3-cyclopentyl-3-hydrazinylpropionitrile or a hydrate of a salt of 3-cyclopentyl-3-hydrazinylpropionitrile with an aqueous base, extraction is performed with dichloromethane, and a test sample solution is obtained from the dichloromethane layer; or

[0012] Method S4: 3-cyclopentyl-3-hydrazinylpropionitrile is dissolved in dichloromethane to obtain a test sample solution.

[0013] In some embodiments, the gas chromatography employs a DB-17 gas chromatography column as the separation chromatographic column for separation; and the detection method further comprises preparation of a test sample solution, wherein the preparation of the test sample solution comprises method S5 or method S6:

[0014] Method S5: after derivatization of 3-cyclopentyl-3-hydrazinylpropionitrile with acetone, a test sample solution is obtained;

[0015] Method S6: after derivatization of a salt of 3-cyclopentyl-3-hydrazinylpropionitrile or a hydrate of a salt of 3-cyclopentyl-3-hydrazinylpropionitrile with acetone, extraction is performed with dichloromethane, and a test sample solution is obtained from the dichloromethane layer.

[0016] In some embodiments, the derivatization is performed under the condition of sealed heating at 60-70°C (such as 60°C, 61°C, 62°C, 63°C, 64°C, 65°C, 66°C, 67°C, 68°C, 69°C or 70°C) for at least 1 h. In some embodiments, the derivatization is performed under the condition of sealed heating at 60-70°C (such as 60°C, 61°C, 62°C, 63°C, 64°C, 65°C, 66°C, 67°C, 68°C, 69°C or 70°C) for 1-3 h (e.g. 1 h, 2 h or 3 h).

[0017] In some embodiments, the reaction formula of the derivatization is as follows:

[0018]

[0019] In some embodiments, the separation column has a column length of 10 m to 60 m. In some embodiments, the separation column has a column length of 10 m, 15 m, 20 m, 25 m, 30 m, 50 m, 55 m, or 60 m.

[0020] In some embodiments, the separation column has an inner diameter of 0.05 mm to 0.53 mm. In some embodiments, the separation column has an inner diameter of 0.05 mm, 0.10 mm, 0.15 mm, 0.25 mm, 0.32 mm, 0.45 mm, or 0.53 mm.

[0021] In some embodiments, the separation column has a film thickness of 0.1 μιη to 1.5 μιη. In some embodiments, the separation column has a film thickness of 0.1 μιη, 0.18 μιη, 0.25 μιη, 0.30 μιη, 0.50 μιη, 1.0 μιη, or 1.5 μιη.

[0022] In some embodiments, the separation column has a column length of 30 m, an inner diameter of 0.25 mm to 0.32 mm, and a film thickness of 0.25 μιη to 0.5 μιη.

[0023] In some embodiments, the CAM gas chromatography column has a column length of 30 m, an inner diameter of 0.25 mm, and a film thickness of 0.5 μιη.

[0024] In some embodiments, the DB-17 gas chromatography column has a column length of 30 m, an inner diameter of 0.32 mm, and a film thickness of 0.25 μιη.

[0025] In some embodiments, the temperature program of the gas chromatography method employs a programmed temperature program, the programmed temperature program comprising one of:

[0026]

[0027] ; or

[0028]

[0029] ; or

[0030]

[0031] ; or

[0032]

[0033] In some embodiments, the gas chromatography employs split injection, and the split ratio of the gas chromatography is 20: 1-10: 1. In some embodiments, the gas chromatography employs split injection, and the split ratio of the gas chromatography is 20: 1, 19: 1, 18: 1, 17: 1, 16: 1, 15: 1, 14: 1, 13: 1, 12: 1, 11: 1, or 10: 1.

[0034] In some embodiments, the carrier gas of the gas chromatography is nitrogen.

[0035] In some embodiments, the flow rate mode of the gas chromatography is constant flow.

[0036] In some embodiments, the column flow rate of the gas chromatography is 1.5 ml / min-2.0 ml / min. In some embodiments, the column flow rate of the gas chromatography is 1.5 ml / min, 1.6 ml / min, 1.7 ml / min, 1.8 ml / min, 1.9 ml / min, or 2.0 ml / min.

[0037] In some embodiments, the detector temperature of the gas chromatography is 250°C-300°C. In some embodiments, the detector temperature of the gas chromatography is 250°C-270°C. In some embodiments, the detector temperature of the gas chromatography is 250°C, 255°C, 260°C, 265°C, 270°C, 275°C, 280°C, 285°C, 290°C, 295°C, or 300°C.

[0038] In some embodiments, the inlet temperature of the gas chromatography is 250°C-300°C. In some embodiments, the inlet temperature of the gas chromatography is 250°C-270°C. In some embodiments, the inlet temperature of the gas chromatography is 250°C, 255°C, 260°C, 265°C, 270°C, 275°C, 280°C, 285°C, 290°C, 295°C, or 300°C.

[0039] In some embodiments, the sampling frequency of the gas chromatography is 10 Hz / min-50 Hz / min. In some embodiments, the sampling frequency of the gas chromatography is 10 Hz / min, 15 Hz / min, 20 Hz / min, 25 Hz / min, 30 Hz / min, 35 Hz / min, 40 Hz / min, 45 Hz / min, or 50 Hz / min. In some embodiments, the sampling frequency of the gas chromatography is 20 Hz / min.

[0040] In some embodiments, the detector of the gas chromatography is a flame ionization detector.

[0041] In some embodiments, the flame ionization detector uses hydrogen as the fuel gas, air as the combustion gas, and nitrogen as the tail gas.

[0042] In some embodiments, the flow rate of the fuel gas is 30 ml / min-50 ml / min. In some embodiments, the flow rate of the fuel gas is 30 ml / min, 35 ml / min, 40 ml / min, 45 ml / min, or 50 ml / min. In some embodiments, the flow rate of the fuel gas is 30 ml / min.

[0043] In some embodiments, the flow rate of the combustion gas is 300 ml / min-450 ml / min. In some embodiments, the flow rate of the combustion gas is 350 ml / min, 360 ml / min, 370 ml / min, 380 ml / min, 390 ml / min, 400 ml / min, 410 ml / min, 420 ml / min, 430 ml / min, 440 ml / min, or 450 ml / min. In some embodiments, the flow rate of the combustion gas is 300 ml / min.

[0044] In some embodiments, the flow rate of the tail gas is 25 ml / min-50 ml / min. In some embodiments, the flow rate of the tail gas is 25 ml / min-30 ml / min. In some embodiments, the flow rate of the tail gas is 25 ml / min, 30 ml / min, 35 ml / min, 40 ml / min, 45 ml / min, or 50 ml / min.

[0045] In some embodiments of the method S1 or method S5, 50 mg-500 mg or 100 mg of 3-cyclopentyl-3-hydrazinylpropionitrile is mixed with 1 ml of the acetone. In some embodiments of the method S1 or method S5, 50 mg, 75 mg, 100 mg, 125 mg, 150 mg, 200 mg, 250 mg, 300 mg, 350 mg, 400 mg, 450 mg, or 500 mg of 3-cyclopentyl-3-hydrazinylpropionitrile is mixed with 1 ml of the acetone.

[0046] In some embodiments, in the method S1 or the method S5, 50 mg-500 mg (e.g., 50 mg, 75 mg, 100 mg, 125 mg, 150 mg, 200 mg, 250 mg, 300 mg, 350 mg, 400 mg, 450 mg, or 500 mg) of 3-cyclopentyl-3-hydrazinylpropionitrile is mixed with 1 ml of the acetone; the derivatization comprises mixing 3-cyclopentyl-3-hydrazinylpropionitrile with acetone, heating at 60 °C-70 °C (e.g., 60 °C, 61 °C, 62 °C, 63 °C, 64 °C, 65 °C, 66 °C, 67 °C, 68 °C, 69 °C, or 70 °C) for at least 1 h, and cooling to room temperature.

[0047] In some embodiments, in the method S1 or the method S5, the room temperature is 15 °C-35 °C (e.g., 15 °C, 20 °C, 25 °C, 30 °C, or 35 °C).

[0048] In some embodiments, in the method S1 or the method S5, the heating time is 1 h-3 h (e.g., 1 h, 2 h, or 3 h).

[0049] In some embodiments, the method S2 or the method S6 comprises: after the derivatization of the salt of 3-cyclopentyl-3-hydrazinylpropionitrile or the hydrate of the salt of 3-cyclopentyl-3-hydrazinylpropionitrile with acetone, extracting with dichloromethane, and taking the dichloromethane layer to obtain a test solution; the derivatization comprises mixing the salt of 3-cyclopentyl-3-hydrazinylpropionitrile or the hydrate of the salt of 3-cyclopentyl-3-hydrazinylpropionitrile with acetone, heating at 60 °C-70 °C (e.g., 60 °C, 61 °C, 62 °C, 63 °C, 64 °C, 65 °C, 66 °C, 67 °C, 68 °C, 69 °C, or 70 °C) for at least 1 h, and cooling to room temperature.

[0050] In some embodiments, in the method S2 or the method S6, 50 mg-500 mg of the salt of 3-cyclopentyl-3-hydrazinylpropionitrile or the hydrate of the salt of 3-cyclopentyl-3-hydrazinylpropionitrile is mixed with 1 ml of the acetone for derivatization. In some embodiments, in the method S2 or the method S6, 50 mg, 75 mg, 100 mg, 125 mg, 150 mg, 200 mg, 250 mg, 300 mg, 350 mg, 400 mg, 450 mg, or 500 mg of the salt of 3-cyclopentyl-3-hydrazinylpropionitrile or the hydrate of the salt of 3-cyclopentyl-3-hydrazinylpropionitrile is mixed with 1 ml of the acetone for derivatization. In some embodiments, in the method S2 or the method S6, 100 mg of the salt of 3-cyclopentyl-3-hydrazinylpropionitrile or the hydrate of the salt of 3-cyclopentyl-3-hydrazinylpropionitrile is mixed with 1 ml of the acetone for derivatization.

[0051] In some embodiments, the sealing heating time in the method S2 or the method S6 is 1 h-3 h. In some embodiments, the sealing heating time in the method S2 or the method S6 is 1 h, 2 h or 3 h.

[0052] In some embodiments, the volume ratio of the acetone to dichloromethane in the method S2 or the method S6 is 1:1-1:5. In some embodiments, the volume ratio of the acetone to dichloromethane in the method S2 or the method S6 is 1:1, 1:2, 1:3, 1:4 or 1:5.

[0053] In some embodiments, the room temperature in the method S2 or the method S6 is 15℃-35℃. In some embodiments, the room temperature in the method S2 or the method S6 is 15℃, 20℃, 25℃, 30℃ or 35℃.

[0054] In some embodiments, the aqueous alkali solution in the method S3 is an aqueous sodium hydroxide solution or an aqueous potassium hydroxide solution, and the concentration of the aqueous sodium hydroxide solution or the aqueous potassium hydroxide solution is 5 mg / ml-20 mg / ml. In some embodiments, the aqueous alkali solution in the method S3 is an aqueous sodium hydroxide solution or an aqueous potassium hydroxide solution, and the concentration of the aqueous sodium hydroxide solution or the aqueous potassium hydroxide solution is 5 mg / ml, 6 mg / ml, 7 mg / ml, 8 mg / ml, 9 mg / ml, 10 mg / ml, 11 mg / ml, 12 mg / ml, 13 mg / ml, 14 mg / ml, 15 mg / ml, 16 mg / ml, 17 mg / ml, 18 mg / ml, 19 mg / ml or 20 mg / ml. In some embodiments, the aqueous alkali solution in the method S3 is an aqueous sodium hydroxide solution or an aqueous potassium hydroxide solution, and the concentration of the aqueous sodium hydroxide solution or the aqueous potassium hydroxide solution is 10 mg / ml.

[0055] In some embodiments, 50 mg-500 mg of the salt of 3-cyclopentyl-3-hydrazinylpropionitrile or the hydrate of the salt of 3-cyclopentyl-3-hydrazinylpropionitrile is mixed with every 1 ml of the aqueous alkali solution in the method S3. In some embodiments, 50 mg, 75 mg, 100 mg, 125 mg, 150 mg, 200 mg, 250 mg, 300 mg, 350 mg, 400 mg, 450 mg or 500 mg of the salt of 3-cyclopentyl-3-hydrazinylpropionitrile or the hydrate of the salt of 3-cyclopentyl-3-hydrazinylpropionitrile is mixed with every 1 ml of the aqueous alkali solution in the method S3. In some embodiments, 100 mg of the salt of 3-cyclopentyl-3-hydrazinylpropionitrile or the hydrate of the salt of 3-cyclopentyl-3-hydrazinylpropionitrile is mixed with every 1 ml of the aqueous alkali solution in the method S3.

[0056] In some embodiments, the volume ratio of the aqueous alkali solution to dichloromethane in the extraction of the method S3 is 1:1-1:5. In some embodiments, the volume ratio of the aqueous alkali solution to dichloromethane in the extraction of the method S3 is 1:1, 1:2, 1:3, 1:4 or 1:5.

[0057] In some embodiments, 50mg-500mg or 100mg of 3-cyclopentyl-3-hydrazinylpropionitrile is dissolved in 1ml of dichloromethane in the method S4. In some embodiments, 50mg, 75mg, 100mg, 125mg, 150mg, 200mg, 250mg, 300mg, 350mg, 400mg, 450mg or 500mg of 3-cyclopentyl-3-hydrazinylpropionitrile is dissolved in 1ml of dichloromethane in the method S4. In some embodiments, 100mg of 3-cyclopentyl-3-hydrazinylpropionitrile is dissolved in 1ml of dichloromethane in the method S4.

[0058] In some embodiments, the separation column is a CAM gas chromatography column, the length of the column is 30m, the inner diameter is 0.25mm, and the film thickness is 0.50μm; the temperature rising program of the gas chromatography is a programmed temperature rising program, and the programmed temperature rising program is as follows:

[0059]

[0060] The gas chromatography adopts split injection, and the split ratio of the gas chromatography is 10:1;

[0061] The carrier gas of the gas chromatography is nitrogen, the flow rate mode of the gas chromatography is constant flow, the column flow rate of the gas chromatography is 2.0ml / min, the detector temperature of the gas chromatography is 270℃, the injection port temperature of the gas chromatography is 250℃, and the sampling frequency of the gas chromatography is 20Hz / min;

[0062] The detector of the gas chromatography is a flame ionization detector, the flame ionization detector uses hydrogen as fuel gas, air as combustion-supporting gas, and nitrogen as tail gas; the flow rate of the fuel gas is 30ml / min, the flow rate of the combustion-supporting gas is 300ml / min, and the flow rate of the tail gas is 25ml / min;

[0063] The detection method further comprises preparation of a test sample solution, and the preparation of the test sample solution comprises:

[0064] Method S1: acetone is used to derivatize 3-cyclopentyl-3-hydrazinylpropionitrile, and then the mixture is heated at 60-70°C for at least 1 h in a sealed state, and then cooled to room temperature to obtain a test solution; 1 ml of the acetone is mixed with 50-500 mg or 100 mg of 3-cyclopentyl-3-hydrazinylpropionitrile; the heating time in the sealed state is 1-3 h; and the room temperature is 15-35°C;

[0065] Method S2: acetone is used to derivatize a salt of 3-cyclopentyl-3-hydrazinylpropionitrile or a hydrate of a salt of 3-cyclopentyl-3-hydrazinylpropionitrile, and then dichloromethane is used to extract the mixture to obtain a test solution; in the method S2, 1 ml of the acetone is mixed with 50-500 mg or 100 mg of a salt of 3-cyclopentyl-3-hydrazinylpropionitrile or a hydrate of a salt of 3-cyclopentyl-3-hydrazinylpropionitrile; the heating time in the sealed state is 1-3 h; the volume ratio of the acetone to dichloromethane is 1:1-1:5; and the room temperature is 15-35°C; or

[0066] Method S3: a salt of 3-cyclopentyl-3-hydrazinylpropionitrile or a hydrate of a salt of 3-cyclopentyl-3-hydrazinylpropionitrile is dissolved in an aqueous alkali solution, and then dichloromethane is used to extract the mixture to obtain a test solution; in the method S3, the aqueous alkali solution is an aqueous sodium hydroxide solution or an aqueous potassium hydroxide solution, the concentration of the aqueous sodium hydroxide solution or the aqueous potassium hydroxide solution is 10 mg / ml, 1 ml of the aqueous sodium hydroxide solution or the aqueous potassium hydroxide solution is mixed with 50-150 mg of a salt of 3-cyclopentyl-3-hydrazinylpropionitrile or a hydrate of a salt of 3-cyclopentyl-3-hydrazinylpropionitrile; in the extraction, the volume ratio of the aqueous sodium hydroxide solution or the aqueous potassium hydroxide solution to dichloromethane is 1:1-1:5; or

[0067] Method S4: 3-cyclopentyl-3-hydrazinylpropionitrile is dissolved in dichloromethane to obtain a test solution; in the method S4, 1 ml of dichloromethane is used to dissolve 50-500 mg or 100 mg of 3-cyclopentyl-3-hydrazinylpropionitrile.

[0068] In some embodiments, the separation column is a DB-17 gas chromatography column, the length of the DB-17 gas chromatography column is 30 m, the inner diameter of the DB-17 gas chromatography column is 0.32 mm, and the film thickness of the DB-17 gas chromatography column is 0.25 μm; the temperature rising program of the gas chromatography is a programmed temperature rising program, and the programmed temperature rising program is as follows:

[0069]

[0070] The gas chromatography uses split injection, and the split ratio of the gas chromatography is 10:1;

[0071] The carrier gas of the gas chromatography is nitrogen; the flow rate mode of the gas chromatography is constant flow; the column flow rate of the gas chromatography is 2.0 ml / min; the detector temperature of the gas chromatography is 270℃; the injection port temperature of the gas chromatography is 250℃; and the sampling frequency of the gas chromatography is 20 Hz / min.

[0072] The detector of the gas chromatography is a flame ionization detector; the flame ionization detector uses hydrogen as fuel gas, air as combustion-supporting gas, and nitrogen as tail gas; the flow rate of the fuel gas is 30 ml / min; the flow rate of the combustion-supporting gas is 300 ml / min; and the flow rate of the tail gas is 25 ml / min.

[0073] The detection method further comprises preparation of a test sample solution, which comprises:

[0074] Method S5: after derivatization of 3-cyclopentyl-3-hydrazinylpropionitrile with acetone, sealed heating at 60-70℃ for at least 1 h, cooling to room temperature to obtain a test sample solution; 50-500 mg or 100 mg of 3-cyclopentyl-3-hydrazinylpropionitrile is mixed with 1 ml of the acetone; the sealed heating time is 1-3 h; and the room temperature is 15-35℃; or

[0075] Method S6: after derivatization of 3-cyclopentyl-3-hydrazinylpropionitrile or a hydrate of a salt of 3-cyclopentyl-3-hydrazinylpropionitrile with acetone, extraction with dichloromethane, and taking the dichloromethane layer to obtain a test sample solution; the derivatization conditions are sealed heating at 60-70℃ for at least 1 h; in the method S6, 50-150 mg of 3-cyclopentyl-3-hydrazinylpropionitrile or a hydrate of a salt of 3-cyclopentyl-3-hydrazinylpropionitrile is mixed with 1 ml of the acetone; and the volume ratio of the acetone to dichloromethane is 1:1-1:5.

[0076] In some embodiments, the structure of the 3-cyclopentyl-3-hydrazinylpropionitrile is:

[0077]

[0078] In some embodiments, the salt of the 3-cyclopentyl-3-hydrazinylpropionitrile is a 3-cyclopentyl-3-hydrazinylpropionitrile tartrate salt:

[0079]

[0080] In some embodiments, the hydrate of the salt of the 3-cyclopentyl-3-hydrazinylpropionitrile is a 3-cyclopentyl-3-hydrazinylpropionitrile tartrate dihydrate:

[0081]

[0082] Advantages

[0083] Compared with the prior art, the present application has at least one of the following advantages:

[0084] (1) The detection method provided by the present application has good separation degree, good peak type, simple operation, simple and fast method.

[0085] (2) The present application can use CAM chromatographic column as gas chromatographic separation column, and use the method S1, method S2, method S3, method S4 or method S5 provided by the present application to prepare the test solution, and then perform chromatographic separation, the target peak and the adjacent chromatographic peak in the obtained chromatogram have no platform peak, the target peak has good peak type, the target peak and the adjacent chromatographic peak are well separated, and have excellent technical effect.

[0086] (3) The present application can use DB-17 chromatographic column as gas chromatographic separation column, and use the method S5 and method S6 test solution provided by the present application, and then perform chromatographic separation, the target peak and the adjacent chromatographic peak in the obtained chromatogram have no platform peak, the target peak has good peak type, the target peak and the adjacent chromatographic peak are well separated, and have excellent technical effect. BRIEF DESCRIPTION OF DRAWINGS

[0087] Figure 1 The chromatogram of the test solution in Example 1.

[0088] Figure 2 The chromatogram of the test solution in Example 2.

[0089] Figure 3 The chromatogram of the test solution in Comparative Example 1.

[0090] Figure 4 The chromatogram of the test solution in Comparative Example 2.

[0091] Figure 5 The chromatogram of the test solution in Comparative Example 3.

[0092] Figure 6 The chromatogram of the test solution in Comparative Example 4.

[0093] Figure 7 The chromatogram of the test solution in Comparative Example 5.

[0094] Figure 8 The chromatogram of the test solution in Comparative Example 6.

[0095] TERMINOLOGY

[0096] The term "room temperature" means ambient temperature, which refers to a temperature of about 10°C to about 35°C, or about 20°C to 30°C, or about 25°C.

[0097] The term "split ratio" means the volume ratio of the air portion to the portion flowing into the chromatographic column after the sample to be measured is gasified, for example, a split ratio of 10:1 means that the volume ratio of the air portion to the portion flowing into the chromatographic column after the sample to be measured is gasified is 10:1.

[0098] In the description of the present specification, the description of the terms "one embodiment", "some embodiments", "an example", "a specific example", or "some examples" and the like means that the specific features, structures, materials or characteristics described in connection with the embodiment or example are included in at least one embodiment or example of the present application. In the present specification, the illustrative expressions of the above terms do not necessarily refer to the same embodiment or example. Also, the specific features, structures, materials or characteristics described can be combined in any appropriate manner in any one or more embodiments or examples. In addition, the person skilled in the art can combine and combine the different embodiments or examples described in the present specification and the features of the different embodiments or examples without contradiction.

[0099] In the following, all the numbers disclosed herein are approximate, whether or not the word "approximately" or "about" is used in connection with such numbers. The value of each number can vary by 1%, 2%, 5%, 7%, 8%, 10%, 15%, or 20% or more. Whenever a number having a value of N is disclosed, any number having a value of N + / - 1%, N + / - 2%, N + / - 3%, N + / - 5%, N + / - 7%, N + / - 8%, N + / - 10%, N + / - 15%, or N + / - 20% is also disclosed, where "+" and "-" mean plus or minus. DETAILED DESCRIPTION

[0100] The person skilled in the art can modify the chromatographic condition parameters as appropriate in light of the content herein. In particular, it is pointed out that all similar substitutions and modifications are obvious to the person skilled in the art and are considered to be included in the present application. The method of the present application has been described by way of preferred embodiments, and the person skilled in the art can obviously make modifications or appropriate changes and combinations to the method described herein without departing from the content, spirit and scope of the present application, to realize and apply the present application technology.

[0101] The main peak described in each embodiment or comparative example of the present application is the peak of the compound 1 obtained after derivatization.

[0102] In order to further understand the present application, the present application will be described in detail below in conjunction with the examples.

[0103] CAM gas chromatographic column: the stationary phase is alkali-modified polyethylene glycol, and the manufacturer is Agilent Technologies.

[0104] DB-17 gas chromatography column: the stationary phase is 50% phenyl-50% dimethylpolysiloxane, and the manufacturer is Agilent Technology Co., Ltd.

[0105] Rtx-5-Amine gas chromatography column: the stationary phase is 5% diphenyl 95% dimethylpolysiloxane, and the manufacturer is Agilent Technology Co., Ltd.

[0106] DB-5 gas chromatography column: the stationary phase is 5% phenyl 95% dimethylpolysiloxane, and the manufacturer is Agilent Technology Co., Ltd.

[0107] Rtx-35 gas chromatography column: the stationary phase is 35%-phenyl 65% dimethylpolysiloxane, and the manufacturer is Agilent Technology Co., Ltd.

[0108] DB-1301 gas chromatography column: the stationary phase is 6% cyanopropyl-phenyl-94% dimethylpolysiloxane, and the manufacturer is Agilent Technology Co., Ltd.

[0109] DB-1 gas chromatography column: the stationary phase is 100% dimethylpolysiloxane, and the manufacturer is Agilent Technology Co., Ltd.

[0110] Example 1: using CAM gas chromatography column as separation chromatography column

[0111] 1. Chromatographic conditions

[0112] Chromatography column: CAM chromatography column, specification 30m*0.25mm, 0.5μm;

[0113] Inlet temperature: 250℃;

[0114] Split ratio: 10:1;

[0115] Carrier gas: nitrogen;

[0116] Flow rate mode: constant flow;

[0117] Column flow rate: 2.0ml / min;

[0118] Injection volume: 1.0ul;

[0119] Temperature rising program:

[0120]

[0121] Detector: FID (flame ionization detector);

[0122] Detector temperature: 270℃;

[0123] Using hydrogen as fuel gas, the fuel gas flow is 30ml / min; using air as combustion-supporting gas, the combustion-supporting gas flow is 300ml / min; using nitrogen as tail gas, the tail gas flow is 25ml / min;

[0124] Sampling frequency: 20 Hz / min.

[0125] 2. Solution preparation

[0126] NaOH aqueous solution: dissolve NaOH in water, 10 mg NaOH is dissolved in 1 ml to obtain NaOH aqueous solution.

[0127] Blank solution: mix NaOH aqueous solution (NaOH concentration is 10 mg / ml) with dichloromethane at a volume ratio of 1:2, extract, take the lower layer to obtain the blank solution.

[0128] Test solution: dissolve 3-cyclopentyl-3-hydrazinylpropionitrile tartrate dihydrate in NaOH aqueous solution (NaOH concentration is 10 mg / ml), then extract with dichloromethane, take the lower layer (i.e. dichloromethane layer) to obtain the test solution (after extraction, the tartrate and water molecules are removed after dissolving in NaOH aqueous solution, to obtain the test solution containing 3-cyclopentyl-3-hydrazinylpropionitrile), wherein 100 mg 3-cyclopentyl-3-hydrazinylpropionitrile tartrate dihydrate is dissolved in 1 ml NaOH aqueous solution, and the volume ratio of NaOH aqueous solution to dichloromethane is 1:2.

[0129] 3. Detection

[0130] Take the blank solution and the test solution respectively, and detect them according to the chromatographic conditions in this example, and record the chromatogram.

[0131] 4. Results and conclusions

[0132] Results: see Figure 1 and Table 1.

[0133] Table 1: detection results of the detection method of Example 1

[0134]

[0135]

[0136] Conclusion: there is no plateau peak between the target peak and the adjacent chromatographic peak, the target peak has good peak shape, and the target peak is well separated from the adjacent chromatographic peak.

[0137] Example 2: DB-17 gas chromatography column is used as the separation chromatography column

[0138] 1. Chromatographic conditions

[0139] Chromatography column: DB-17 chromatography column, specification is 30 m*0.32 mm, 0.25 μm;

[0140] Injection port temperature, split ratio, carrier gas, flow mode, column flow, injection volume, temperature program, detector, detector temperature, fuel gas and its flow rate, combustion gas and its flow rate, tail gas and its flow rate, sampling frequency: same as in Example 1.

[0141] 2. Solution preparation

[0142] Blank solution: acetone was heated at 70°C for 1 h, cooled to room temperature, extracted with dichloromethane, and the lower layer was taken to obtain the blank solution, wherein the volume ratio of acetone to dichloromethane was 1:2.

[0143] Test solution: 3-cyclopentyl-3-hydrazinylpropionitrile tartrate dihydrate was dissolved in acetone, heated at 70°C for 1 h (3-cyclopentyl-3-hydrazinylpropionitrile was derivatized, and the derivatization process is shown in the following reaction formula to obtain compound 1), cooled to room temperature, extracted with dichloromethane, and the lower layer (i.e. the dichloromethane layer) was taken to obtain the test solution (after extraction, the tartrate and water molecules were removed, and the test solution contained compound 1); wherein 100 mg of 3-cyclopentyl-3-hydrazinylpropionitrile tartrate dihydrate was dissolved in 1 ml of acetone, and the volume ratio of acetone to dichloromethane was 1:2.

[0144]

[0145] 3. Detection

[0146] The blank solution and each test solution were detected according to the chromatographic conditions in this example, and the chromatograms were recorded.

[0147] 4. Results and conclusions

[0148] Results: see Figure 2 and Table 2.

[0149] Table 2: Detection results of the detection method of Example 2

[0150]

[0151] Conclusion: There is no plateau peak between the target peak and the adjacent chromatographic peak, the target peak has a good peak shape, and the target peak is well separated from the adjacent chromatographic peak.

[0152] Comparative Examples 1-4: Investigation of chromatographic column

[0153] 1. Chromatographic conditions

[0154] Chromatographic column: see Table 3.

[0155] Injection port temperature, split ratio, carrier gas, flow mode, column flow, injection volume, temperature program, detector, detector temperature, fuel gas and its flow rate, combustion gas and its flow rate, tail gas and its flow rate, sampling frequency: same as in Example 1.

[0156] 2. Solution preparation

[0157] The same as Example 1.

[0158] 3. Detection

[0159] The blank solution and the test solution were respectively detected according to the chromatographic conditions in the present comparative example, and the chromatogram was recorded.

[0160] 4. Results and conclusion

[0161] Results: see Figures 3-6 and Table 3.

[0162] Table 3: detection results of Comparative Example 1-Comparative Example 4 detection method

[0163]

[0164] Conclusion: using the chromatographic column described in Comparative Example 1-Comparative Example 4 for separation, the peak shape of the target is poor, and there is a platform peak between the target and the adjacent chromatographic peak.

[0165] Comparative Example 5:

[0166] 1. Chromatographic conditions

[0167] Chromatographic column: DB-1 gas chromatographic column, specification 30m*0.32mm, 1.5μm;

[0168] Injection port temperature, split ratio, carrier gas, flow rate mode, column flow rate, injection volume, detector, detector temperature, fuel gas and its flow rate, combustion supporting gas and its flow rate, tail gas and its flow rate, sampling frequency: the same as Example 1.

[0169] Temperature rising program:

[0170]

[0171] 2. Solution preparation

[0172] Diluent / blank solution: dichloromethane;

[0173] Preparation of test solution: 3-cyclopentyl-3-hydrazinylpropionitrile was prepared into a solution of 100mg / mL with diluent to obtain the test solution.

[0174] 3. Detection

[0175] The blank solution and the test solution were respectively detected according to the chromatographic conditions in the present comparative example, and the chromatogram was recorded.

[0176] 4. Results and conclusion

[0177] Results: see Figure 7 (main peak peak time 13.291min).

[0178] Conclusion: Using the chromatographic conditions and solution preparation method described in Comparative Example 5, a plateau peak appears between the target peak and the adjacent chromatographic peak in the obtained spectrum, affecting the integration of the target peak.

[0179] Comparative Example 6: Investigation of Test Solution Preparation Method (without acetone derivatization)

[0180] 1. Chromatographic Conditions

[0181] The same as in Example 2.

[0182] 2. Solution Preparation

[0183] Diluent / Blank Solution: Dichloromethane;

[0184] Test Solution Preparation: 3-cyclopentyl-3-hydrazinylpropionitrile was prepared into a 100 mg / mL solution with diluent to obtain the test solution.

[0185] 3. Detection

[0186] The blank solution and the test solution were respectively detected according to the chromatographic conditions in this comparative example, and the chromatogram was recorded.

[0187] 4. Results and Conclusion

[0188] Results: See Figure 8 and Table 4.

[0189] Table 4: Detection Results of Comparative Example 6

[0190]

[0191] Conclusion: A plateau peak appears between the target peak and the adjacent chromatographic peak, affecting the integration of the target peak, indicating that when the DB-17 gas chromatography column is used as the separation chromatography column, if the test solution is not subjected to acetone derivatization, the separation effect is poor, and excellent separation effect cannot be obtained.

[0192] The method of the present application has been described by preferred embodiments, and relevant personnel can obviously make changes or appropriate changes and combinations to the methods and applications described herein within the content, spirit and scope of the present application to realize and apply the present application technology. Those skilled in the art can refer to the content herein to appropriately improve the parameters for implementation. It is particularly pointed out that all similar substitutions and changes are obvious to those skilled in the art, and they are considered to be included in the present application.

Claims

1. A method for determining the purity of 3-cyclopentyl-3-hydrazinonitrile or its salt or its hydrate, characterized in that, The detection method includes: Prepare the test solution and detect it using gas chromatography; The preparation method of the test solution includes: derivatizing 3-cyclopentyl-3-hydrazinopropionitrile with acetone to obtain the test solution; or derivatizing the salt of 3-cyclopentyl-3-hydrazinopropionitrile or the hydrate of the salt of 3-cyclopentyl-3-hydrazinopropionitrile with acetone, extracting with dichloromethane, and taking the dichloromethane layer to obtain the test solution; or dissolving the salt of 3-cyclopentyl-3-hydrazinopropionitrile or the aqueous solution of the salt of 3-cyclopentyl-3-hydrazinopropionitrile with acetone in an alkaline aqueous solution, extracting with dichloromethane, and taking the dichloromethane layer to obtain the test solution.

2. The detection method according to claim 1, characterized in that, The gas chromatography method uses a CAM gas chromatography column as the separation column for separation. The detection method further includes the preparation of a test solution, which includes method S1, method S2, method S3, or method S4. Method S1: 3-Cyclopentyl-3-hydrazinonitrile is derivatized with acetone to obtain the test solution; or Method S2: After derivatizing the salt of 3-cyclopentyl-3-hydrazinopropionitrile with acetone or the hydrate of the salt of 3-cyclopentyl-3-hydrazinopropionitrile with acetone, extract with dichloromethane, collect the dichloromethane layer, and obtain the test solution; or Method S3: Dissolve the salt of 3-cyclopentyl-3-hydrazinopropionitrile in an alkaline aqueous solution or the hydrate of the salt of 3-cyclopentyl-3-hydrazinopropionitrile derivatized in acetone, extract with dichloromethane, and collect the dichloromethane layer to obtain the test solution; or Method S4: Dissolve 3-cyclopentyl-3-hydrazinopropionitrile in dichloromethane to obtain the test solution; or The gas chromatography method uses a DB-17 gas chromatographic column as the separation column for separation; the detection method further includes the preparation of a test solution, which includes method S5 or method S6: Method S5: 3-Cyclopentyl-3-hydrazinopropionitrile was derivatized with acetone to obtain the test solution; Method S6: After derivatizing the salt of 3-cyclopentyl-3-hydrazinopropionitrile with acetone or the hydrate of the salt of 3-cyclopentyl-3-hydrazinopropionitrile with acetone, extract with dichloromethane, take the dichloromethane layer, and obtain the test solution.

3. The detection method according to any one of claims 1-2, The length of the separation chromatographic column is 10m-60m; and / or The inner diameter of the separation chromatographic column is 0.05 mm to 0.53 mm; and / or The membrane thickness of the separation chromatographic column is 0.1 μm-1.5 μm; and / or The separation chromatographic column has a length of 30 m, an inner diameter of 0.25 mm-0.32 mm, and a film thickness of 0.25 μm; and / or The CAM gas chromatography column has a length of 30 m, an inner diameter of 0.25 mm, and a film thickness of 0.5 μm; and / or The DB-17 gas chromatographic column has a length of 30m, an inner diameter of 0.32mm, and a film thickness of 0.25μm.

4. The detection method according to any one of claims 1-3, wherein the temperature program of the gas chromatography is a temperature programmable program, and the temperature programmable program includes one of the following: ； or ； or ； or 5. The detection method according to any one of claims 1-4, wherein the gas chromatography employs split injection, and the split ratio of the gas chromatography is 20:1-10:1; and / or The carrier gas for the gas chromatography method is nitrogen; and / or The flow rate mode of the gas chromatography is constant flow; and / or The column flow rate for the gas chromatography method is 1.5 ml / min - 2.0 ml / min; and / or The detector temperature for the gas chromatography method is 250℃-300℃, or 250℃-270℃; and / or The injection port temperature for the gas chromatography method is 250℃-300℃, or 250℃-270℃; and / or The sampling frequency of the gas chromatography method is 10 Hz / min-50 Hz / min.

6. The detection method according to any one of claims 1-5, wherein the detector of the gas chromatography is a flame ionization detector; and / or The flame ionization detector uses hydrogen as the fuel gas, air as the combustion-supporting gas, and nitrogen as the tail gas; and / or The gas flow rate is 30 ml / min-50 ml / min or 30 ml / min; and / or The flow rate of the combustion-supporting gas is 300 ml / min-450 ml / min or 300 ml / min; and / or The flow rate of the tail gas is 25 ml / min-50 ml / min or 25 ml / min-30 ml / min.

7. The detection method according to any one of claims 2-6, wherein in method S1 or method S5, each 1 ml of acetone is mixed with 50 mg-500 mg or 100 mg of 3-cyclopentyl-3-hydrazinopropionitrile; Optionally, in method S1 or method S5, each 1 ml of acetone is mixed with 50 mg-500 mg or 100 mg of 3-cyclopentyl-3-hydrazinopropionitrile; the derivatization includes mixing 3-cyclopentyl-3-hydrazinopropionitrile with acetone, heating in a sealed container at 60°C-70°C for at least 1 hour, and cooling to room temperature; Optionally, in method S1 or method S5, the room temperature is 15℃-35℃; Optionally, in method S1 or method S5, the sealing heating time is 1h-3h; Optionally, in method S3, the alkaline aqueous solution is an aqueous solution of sodium hydroxide or potassium hydroxide, and the concentration of the aqueous solution of sodium hydroxide or potassium hydroxide is 5 mg / ml-20 mg / ml or 10 mg / ml. Optionally, in method S3, each 1 ml of the alkaline aqueous solution is mixed with 50 mg-500 mg or 100 mg of a salt of 3-cyclopentyl-3-hydrazinopropionitrile or a hydrate of the salt of 3-cyclopentyl-3-hydrazinopropionitrile; Optionally, in the extraction of method S3, the volume ratio of the alkaline aqueous solution to dichloromethane is 1:1 to 1:5; Optionally, in method S4, 50 mg-500 mg or 100 mg of 3-cyclopentyl-3-hydrazinopropionitrile is dissolved in 1 ml of dichloromethane; Optionally, method S2 or method S6 includes: The salt of 3-cyclopentyl-3-hydrazinopropionitrile or the hydrate of the salt of 3-cyclopentyl-3-hydrazinopropionitrile is derivatized with acetone, then extracted with dichloromethane, and the dichloromethane layer is collected to obtain the test solution; the derivatization includes mixing the salt of 3-cyclopentyl-3-hydrazinopropionitrile or the hydrate of the salt of 3-cyclopentyl-3-hydrazinopropionitrile with acetone, heating in a sealed container at 60°C-70°C for at least 1 hour, and then cooling to room temperature; Optionally, in method S2 or method S6, each 1 ml of the acetone is mixed with 50 mg-500 mg or 100 mg of a salt of 3-cyclopentyl-3-hydrazinopropionitrile or a hydrate of the salt of 3-cyclopentyl-3-hydrazinopropionitrile. Optionally, the sealing heating time in method S2 or method S6 is 1h-3h; Optionally, in method S2 or method S6, the volume ratio of acetone to dichloromethane is 1:1 to 1:5; Optionally, in method S2 or method S6, the room temperature is 15℃-35℃.

8. The detection method according to any one of claims 1-7, wherein the separating chromatographic column is a CAM gas chromatographic column, the CAM gas chromatographic column having a column length of 30 m, an inner diameter of 0.25 mm, and a film thickness of 0.50 μm; the temperature program of the gas chromatography method adopts a programmed temperature program, the programmed temperature program being as follows: ； The gas chromatography method employs split injection, and the split ratio of the gas chromatography method is 10:

1. The carrier gas in the gas chromatography is nitrogen; the flow mode of the gas chromatography is constant flow; the column flow rate of the gas chromatography is 2.0 ml / min; the detector temperature of the gas chromatography is 270℃; the injection port temperature of the gas chromatography is 250℃; and the sampling frequency of the gas chromatography is 20 Hz / min. The detector used in the gas chromatography method is a flame ionization detector; the flame ionization detector uses hydrogen as the fuel gas, air as the combustion-supporting gas, and nitrogen as the make-up gas; the flow rate of the fuel gas is 30 ml / min; the flow rate of the combustion-supporting gas is 300 ml / min; and the flow rate of the make-up gas is 25 ml / min. The detection method further includes the preparation of a test solution, wherein the preparation of the test solution includes: Method S1: After derivatizing 3-cyclopentyl-3-hydrazinopropionitrile with acetone, the mixture is heated in a sealed container at 60℃-70℃ for at least 1 hour, and then cooled to room temperature to obtain the test solution; each 1 ml of the acetone is mixed with 50 mg-500 mg or 100 mg of 3-cyclopentyl-3-hydrazinopropionitrile; the sealed heating time is 1 hour-3 hours; the room temperature is 15℃-35℃; Method S2: After derivatizing the salt of 3-cyclopentyl-3-hydrazinopropionitrile with acetone or the hydrate of the salt of 3-cyclopentyl-3-hydrazinopropionitrile with acetone, extract with dichloromethane, and collect the dichloromethane layer to obtain the test solution; in Method S2, each 1 ml of the acetone is mixed with 50 mg-500 mg or 100 mg of the salt of 3-cyclopentyl-3-hydrazinopropionitrile or the hydrate of the salt of 3-cyclopentyl-3-hydrazinopropionitrile; the sealed heating time is 1 h-3 h; the volume ratio of acetone to dichloromethane is 1:1-1:5; the room temperature is 15℃-35℃; or Method S3: Dissolve the salt of 3-cyclopentyl-3-hydrazinopropionitrile in an alkaline aqueous solution or derivatize the hydrate of the salt of 3-cyclopentyl-3-hydrazinopropionitrile with acetone, extract with dichloromethane, and collect the dichloromethane layer to obtain the test solution; in Method S3, the alkaline aqueous solution is an aqueous solution of sodium hydroxide or potassium hydroxide, and the concentration of the aqueous solution of sodium hydroxide or potassium hydroxide is 10 mg / ml; each 1 ml of the aqueous solution of sodium hydroxide or potassium hydroxide is mixed with 50 mg-150 mg of the hydrate of the salt of 3-cyclopentyl-3-hydrazinopropionitrile; in the extraction, the volume ratio of the aqueous solution of sodium hydroxide or potassium hydroxide to the hydrate of dichloromethane is 1:1-1:5; or Method S4: Dissolve 3-cyclopentyl-3-hydrazinopropionitrile in dichloromethane to obtain a test solution; in Method S4, 50mg-500mg or 100mg of 3-cyclopentyl-3-hydrazinopropionitrile is dissolved in 1ml of dichloromethane.

9. The detection method according to any one of claims 1-8, wherein the separating chromatographic column is a DB-17 gas chromatographic column, the DB-17 gas chromatographic column having a column length of 30 m, an inner diameter of 0.32 mm, and a film thickness of 0.25 μm; the temperature program of the gas chromatography method adopts a programmed temperature program, the programmed temperature program being as follows: ； The gas chromatography method employs split injection, and the split ratio of the gas chromatography method is 10:

1. The carrier gas in the gas chromatography is nitrogen; the flow mode of the gas chromatography is constant flow; the column flow rate of the gas chromatography is 2.0 ml / min; the detector temperature of the gas chromatography is 270℃; the injection port temperature of the gas chromatography is 250℃; and the sampling frequency of the gas chromatography is 20 Hz / min. The detector used in the gas chromatography method is a flame ionization detector; the flame ionization detector uses hydrogen as the fuel gas, air as the combustion-supporting gas, and nitrogen as the make-up gas; the flow rate of the fuel gas is 30 ml / min; the flow rate of the combustion-supporting gas is 300 ml / min; and the flow rate of the make-up gas is 25 ml / min. The detection method further includes the preparation of a test solution, wherein the preparation of the test solution includes: Method S5: After derivatizing 3-cyclopentyl-3-hydrazinopropionitrile with acetone, heat in a sealed container at 60℃-70℃ for at least 1 hour, then cool to room temperature to obtain the test solution; each 1 ml of the acetone is mixed with 50 mg-500 mg or 100 mg of 3-cyclopentyl-3-hydrazinopropionitrile; the sealed heating time is 1 hour-3 hours; the room temperature is 15℃-35℃; or Method S6: After derivatizing the salt of 3-cyclopentyl-3-hydrazinopropionitrile with acetone or the hydrate of the salt of 3-cyclopentyl-3-hydrazinopropionitrile with acetone, extract with dichloromethane, and take the dichloromethane layer to obtain the test solution; the derivatization conditions are sealed heating at 60℃-70℃ for at least 1 hour; in Method S6, each 1 ml of the acetone is mixed with 50 mg-150 mg of the salt of 3-cyclopentyl-3-hydrazinopropionitrile or the hydrate of the salt of 3-cyclopentyl-3-hydrazinopropionitrile; the volume ratio of the acetone to the dichloromethane is 1:1-1:

5.

10. The detection method according to any one of claims 1-9, wherein the structure of the 3-cyclopentyl-3-hydrazinonitrile is: and / or The salt of the 3-cyclopentyl-3-hydrazinopropionitrile is 3-cyclopentyl-3-hydrazinopropionitrile tartrate: and / or The hydrate of the salt of 3-cyclopentyl-3-hydrazinopropionitrile is 3-cyclopentyl-3-hydrazinopropionitrile tartrate dihydrate:

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